4-alkyl 1-(3-methoxy-2-propen-1-yl) benzene compounds and their use in perfume compositions

ABSTRACT

The present invention is directed to novel 4-alkyl 1-(3-methoxy-2-propen-1-yl)benzene compounds and a method of improving, enhancing or modifying a fragrance formulation through the addition of an olfactory acceptable amount of the novel compounds.

FIELD OF THE INVENTION

The present invention relates to new chemical entities and theincorporation and use of the new chemical entities as fragrancematerials.

BACKGROUND OF THE INVENTION

There is an ongoing need in the fragrance industry to provide newchemicals to give perfumers and other persons the ability to create newfragrances for perfumes, colognes and personal care products. Those withskill in the art appreciate how small differences in chemical structurescan result in unexpected and significant differences in odor, notes andcharacteristics of molecules. These variations allow perfumers and otherpersons to apply new compounds in creating new fragrances. For example,benzene compounds that differ slightly in substituents possesscompletely different odor profiles [Ishikawa, et al., InternationalJournal of Quantum Chemistry 79: 101-108 (2000)]. In the case oftert-butyl cyclohexanes, the odor is said to be dependent on thecompounds' conformation and therefore analogs adopting same conformationpossess similar odor. Accordingly, many trans-compounds are shown toshare pronounced urine-perspiration-type odor, while the correspondingcis-compounds are odorless or at the most possess weak and undefinableflowery or woody odor. However, some other trans- and cis-tert-butylcyclohexanes are shown to possess opposite sensory activities [Ohloff,et al., Helvetica Chimica Acta 66, Fasc. 5: 1343-1354 (1983)]. Thus, itis hard for those with skill in the art to predict a given structurewould be effective in sensory activities. Identifying desirablefragrance chemicals continues to pose difficult challenges.

SUMMARY OF THE INVENTION

The present invention provides novel chemicals and their unexpectedadvantageous use in enhancing, improving or modifying the fragrance ofperfumes, colognes, toilet waters, personal products and the like.

In one embodiment of the present invention, novel compounds representedby Formula I are provided:

wherein R represents a C₁-C₄ alkyl group and R′ represents hydrogen ormethyl.

In another embodiment of the present invention, a method of improving,enhancing or modifying a fragrance formulation through the addition ofan olfactory acceptable amount of a Formula I compound is provided.

In another embodiment of the present invention, novel compoundsrepresented by Formula II are provided:

wherein R represents a C₁-C₄ alkyl group.

In another embodiment of the present invention, a method of improving,enhancing or modifying a fragrance formulation through the addition ofan olfactory acceptable amount of a Formula II compound is provided.

In another embodiment of the present invention, novel compoundsrepresented by Formula III are provided:

wherein R″ represents a C₂-C₄ alkyl group.

In another embodiment of the present invention, a method of improving,enhancing or modifying a fragrance formulation through the addition ofan olfactory acceptable amount of a Formula III compound is provided.

These and other embodiments of the present invention will be apparent byreading the following specification.

DETAILED DESCRIPTION OF THE INVENTION

It is known to those with the skill in the art that Formula I as definedabove provides the following novel compounds:

Those with the skill in the art will recognize that:

Formula IV represents 4-methyl 1-(3-methoxy-2-propen-1-yl)benzene;

Formula V represents 4-ethyl 1-(3-methoxy-2-propen-1-yl)benzene;

Formula VI represents 4-propyl 1-(3-methoxy-2-propen-1-yl)benzene;

Formula VII represents 4-isopropyl 1-(3-methoxy-2-propen-1-yl)benzene;

Formula VIII represents 4-butyl 1-(3-methoxy-2-propen-1-yl)benzene;

Formula IX represents 4-sec-butyl 1-(3-methoxy-2-propen-1-yl)benzene;

Formula X represents 4-isobutyl 1-(3-methoxy-2-propen-1-yl)benzene;

Formula XI represents 4-tert-butyl 1-(3-methoxy-2-propen-1-yl)benzene;

Formula XII represents 4-methyl (3-methoxy-2-methylallyl)benzene;

Formula XIII represents 4-ethyl (3-methoxy-2-methylallyl)benzene;

Formula XIV represents 4-propyl (3-methoxy-2-methylallyl)benzene;

Formula XV represents 4-isopropyl (3-methoxy-2-methylallyl)benzene;

Formula XVI represents 4-butyl (3-methoxy-2-methylallyl)benzene;

Formula XVII represents 4-sec-butyl (3-methoxy-2-methylallyl)benzene;

Formula XVIII represents 4-isobutyl (3-methoxy-2-methylallyl)benzene;and

Formula XIX represents 4-tert-butyl (3-methoxy-2-methylallyl)benzene.

The compounds of the present invention can be prepared from3-(4-alkyl-phenyl)-propionaldehydes, which are first synthesized via theHoaglin-Hirsch reaction using corresponding 4-alkyl benzaldehydes(commercially available from Mitsubishi Gas Chemical Company, Inc.). Thereaction steps can be depicted by general Schemes 1 and 2 shown asfollows:

wherein R is defined as above;

R₁, R₂, and R₃ represent independently methyl or ethyl;

TMOF represents trimethyl orthoformate; and

Pd/C represents palladium carbon catalyst.

Those with skill in the art will recognize that the 1,4-substitutedaromatic rings contained in the compounds of the present invention giverise to a number of trans- and cis-isomers. It is intended herein thatthe compounds described herein include isomeric mixtures of suchcompounds, as well as those isomers that may be separated usingtechniques known to those having skill in the art. Suitable techniquesinclude chromatography such as high performance liquid chromatography,referred to as HPLC, and particularly gel chromatography and solid phasemicroextraction, referred to as SPME.

The use of the compounds of the present invention is widely applicablein current perfumery products, including the preparation of perfumes andcolognes, the perfuming of personal care products such as soaps, showergels, and hair care products, fabric care products as well as airfresheners and cosmetic preparations. These compounds can also be usedto perfume cleaning agents, such as, but not limited to detergents,dishwashing materials, scrubbing compositions, window cleaners and thelike. In these preparations, the compounds of the present invention canbe used alone or in combination with other perfuming compositions,solvents, adjuvants and the like. The nature and variety of the otheringredients that can also be employed are known to those with skill inthe art.

Many types of fragrances can be employed in the present invention, theonly limitation being the compatibility with the other components beingemployed. Suitable fragrances include but are not limited to fruits suchas almond, apple, cherry, grape, pear, pineapple, orange, strawberry,raspberry; musk, flower scents such as lavender-like, rose-like,iris-like, carnation-like. Other pleasant scents include herbal andwoodland scents derived from pine, spruce and other forest smells.Fragrances may also be derived from various oils, such as essentialoils, or from plant materials such as peppermint, spearmint and thelike. A list of suitable fragrances is provided in U.S. Pat. No.4,534,891, the contents of which are incorporated by reference as if setforth in its entirety. Another source of suitable fragrances is found inPerfumes, Cosmetics and Soaps, Second Edition, edited by W. A. Poucher,1959. Among the fragrances provided in this treatise are acacia, cassie,chypre, cyclamen, fern, gardenia, hawthorn, heliotrope, honeysuckle,hyacinth, jasmine, lilac, lily, magnolia, mimosa, narcissus, freshly-cuthay, orange blossom, orchid, reseda, sweet pea, trefle, tuberose,vanilla, violet, wallflower, and the like.

Olfactory acceptable amount is understood to mean the amount of acompound in a fragrance formulation, wherein the compound willcontribute its individual olfactory characteristics. However, theolfactory effect of the fragrance formulation will be the sum of effectof each of the fragrance ingredients. Thus, the compounds of the presentinvention can be used to improve or enhance the aroma characteristics ofthe fragrance formulation, or by modifying the olfactory reactioncontributed by other ingredients in the formulation. The olfactoryacceptable amount may vary depending on many factors including otheringredients, their relative amounts and the olfactory effect that isdesired.

The amount of the compounds of the present invention employed in afragrance formulation varies from about 0.005 to about 70 weightpercent, preferably from 0.005 to about 10 weight percent, morepreferably from about 0.5 to about 8 weight percent, and even morepreferably from about 1 to about 7 weight percent. Those with skill inthe art will be able to employ the desired amount to provide desiredfragrance effect and intensity. In addition to the compounds of thepresent invention, other materials can also be used in conjunction withthe fragrance formulation. Well known materials such as surfactants,emulsifiers, polymers to encapsulate the fragrance can also be employedwithout departing from the scope of the present invention.

When used in a fragrance formulation, the compounds of the presentinvention provide unexpected strong muguet and green characteristics andmake the fragrance formulation more desirable and noticeable. The odorqualities found in the compounds of the present invention assist inbeautifying and enhancing the finished accord and improve theperformance of other materials in the fragrance formulation.

The following are provided as specific embodiments of the presentinvention. Other modifications of this invention will be readilyapparent to those skilled in the art. Such modifications are understoodto be within the scope of this invention. As used herein all percentagesare weight percent unless otherwise noted, ppm is understood to standfor parts per million, L is understood to be liter, mL is understood tobe milliliter, Kg is understood to be kilogram, g is understood to begram, and mmHg be millimeters (mm) of mercury (Hg). IFF as used in theexamples is understood to mean International Flavors & Fragrances Inc.,New York, N.Y., USA.

Example I

Preparation of 3-(4-propyl-phenyl)-propionaldehyde: A reaction flask wascharged with 4-propyl benzaldehyde (1.064 Kg, commercially availablefrom Mitsubishi Gas Chemical Company, Inc.), methanol (500 mL), andtrimethyl orthoformate (TMOF) (1.144 Kg, commercially available fromSigma-Aldrich, Inc.). The reaction mass was cooled to −10 to 0° C. andhydrochloric acid (37%, 1 g) was added in one portion. The reaction wasinstantaneous and the temperature was allowed to rise to 25° C. for over30 minutes. The reaction mass was then quenched with sodium acetate (20g) and the solvent was removed by evaporation. The crude intermediateproduct 1-dimethoxymethyl-4-propyl-benzene (1.388 Kg) was obtained andcharged to a second reaction flask at 25° C. Boron trifluride etherate(1 g, commercially available from Sigma-Aldrich, Inc.) was added. Ethylvinyl ether (684 g, commercially available from Sigma-Aldrich, Inc.) wasthen fed for over 4 hours with the temperature maintained at 25-30° C.The reaction mass was quenched with saturated sodium carbonate (500 mL).The crude intermediate products methoxy ethoxy acetals were obtained,which were contained in the organic layer and confirmed by NMR analysis.Crude methoxy ethoxy acetals were hydrolyzed in the presence of water(500 mL) containing hydrochloric acid (37%, 50 g) at 90° C. for 5 hoursand further catalytically hydrogenated in 2-propanol (200 mL) usingpalladium on carbon (5%, 1 g) and hydrogen in a 1 L zipper autoclave toprovide the product 3-(4-propyl-phenyl)-propionaldehyde (1.008 Kg),which had a boiling point of 115° C. at a pressure of 6 mmHg.

The NMR analysis of the intermediate products methoxy ethoxy acetals wasthe following:

¹HNMR: 0.94 ppm (t, 3H, J=7.02 Hz), 1.13-1.27 ppm (m, 9H), 1.529-1.68ppm (m, 2H), 1.84-1.91 ppm (m, 1H), 2.06-2.14 ppm (m, 1H), 2.55-2.59 ppm(m, 2H), 2.66 ppm (t, 2H, J=7.59 Hz), 3.17 ppm (s, 3H), 3.30 ppm (s,3H), 3.33 ppm (s, 3H), 3.35-3.67 ppm (m, 6H), 4.19-4.60 ppm (m, 2H),7.15 ppm (d, 2H, J=5.94 Hz), 7.21 ppm (d, 2H, J=7.33 Hz), 7.32 ppm (d,2H, J=7.85 Hz), 7.78 ppm (d, 2H, J=7.94 Hz), 9.95 ppm (s, 1H).

The NMR analysis of 3-(4-propyl-phenyl)-propionaldehyde was thefollowing:

¹HNMR: 0.93 ppm (t, 3H, J=7.34 Hz), 1.62 ppm (m, 2H, J=7.52 Hz), 2.55ppm (t, 2H, J=7.66 Hz), 2.75 ppm (t, 2H, J=7.56 Hz), 2.92 ppm (t, 2H,J=7.56 Hz), 7.10 ppm (s, 4H), 9.81 ppm (s, 1H)

The compound 3-(4-propyl-phenyl)-propionaldehyde was described as havingfloral, muguet, and green notes.

Example II

Preparation of 4-propyl 1-(3-methoxy-2-propen-1-yl)benzene (Formula IV):A reaction flask was charged with 3-(4-propyl-phenyl)-propionaldehyde(147 g, prepared as above), methanol (500 mL), and TMOF (90 g). Thereaction mass was cooled to 0° C. and hydrochloric acid (37%, 1 g) wasadded in one portion. The reaction was exothermic and the temperaturerose to 23° C. The reaction mass was quenched with sodium methoxide inmethanol (25%, 10 g) and the solvent was removed by evaporation. Thecrude intermediate product 3-(4-propyl-phenyl)-propionaldehydedimethylacetal was provided and confirmed by the NMR analysis.3-(4-Propyl-phenyl)-propionaldehyde dimethylacetal was further treatedwith phosphoric acid (10 g) and pyridine (8 g) at 200° C. The reactionmass was aged for 4 hours, during which methanol was recovered in a DeanStark trap. The reaction mass was then cooled and washed with aqueoussodium carbonate solution. Fractional distillation of the organic layerafforded the product 4-propyl 1-(3-methoxy-2-propen-1-yl)benzene (80 g),which had a boiling point of 101° C. at a pressure of 3 mmHg.

The NMR analysis of the intermediate product3-(4-propyl-phenyl)-propionaldehyde dimethylacetal was the following:

¹HNMR: 0.93 ppm (t, 3H, J=7.34 Hz), 1.62 ppm (m, 2H, J=7.49 Hz),1.88-1.93 ppm (m, 2H), 2.55 ppm (t, 2H, J=7.66 Hz), 2.62-2.66 ppm (m,2H), 3.33 ppm (s, 6H), 4.37 ppm (t, 1H, J=5.74 Hz), 7.10 ppm (d, 4H,J=1.48 Hz)

The NMR analysis of 4-propyl 1-(3-methoxy-2-propen-1-yl)benzene was thefollowing:

¹HNMR: 0.91 ppm (d, 3H, J=1.85 Hz, of t, J=7.29 Hz), 1.55-1.63 ppm (m,2H), 2.49-2.54 ppm (m, 2H), 3.18 ppm (d, ˜44% of 2H, J=7.29 Hz), 3.37ppm (d, ˜56% of 2H, J=7.55 Hz), 3.42 ppm (s, ˜44% of 3H), 3.51 ppm (s,˜56% of 3H), 4.50-4.55 ppm (m, ˜56% of 1H), 4.84 ppm (d, ˜44% of 1H,J=12.56 Hz, of t, J=7.21 Hz), 5.91 ppm (d, ˜56% of 1H, J=6.09 Hz), 6.34ppm (d, ˜44% of 1H, J=12.58 Hz), 7.02-7.11 ppm (m, 4H)

The compound 4-propyl 1-(3-methoxy-2-propen-1-yl)benzene was describedas having muguet, green, and fatty notes.

Example III

Preparation of 4-methyl 1-(3-methoxy-2-propen-1-yl)benzene (Formula II):4-Methyl 1-(3-methoxy-2-propen-1-yl)benzene was similarly prepared asdescribed in Examples I and II. First, 4-methyl benzaldehyde (140 g,commercially available from Mitsubishi Gas Chemical Company, Inc.) wasused to obtain 3-(4-methyl-phenyl)-propionaldehyde (130 g) with aboiling point of 120° C. at a pressure of 21 mmHg.3-(4-Methyl-phenyl)-propionaldehyde (225 g) was consequently used toprovide 4-methyl 1-(3-methoxy-2-propen-1-yl)benzene (139 g) with aboiling point of 117° C. at a pressure of 35 mmHg

The NMR analysis of 3-(4-methyl-phenyl)-propionaldehyde was thefollowing:

¹HNMR: 2.29 ppm (s, 3H), 2.69 ppm (t, 2H, J=7.32 Hz), 2.88 ppm (t, 2H,J=7.49 Hz), 7.05 ppm (d, 2H, J=8.04 Hz), 7.07 ppm (d, 2H, J=7.92 Hz),9.74 ppm (s, 1H)

The NMR analysis of 4-methyl 1-(3-methoxy-2-propen-1-yl)benzene was thefollowing:

¹HNMR: 2.28 ppm (s, ˜46% of 3H), 2.29 ppm (s, ˜54% of 3H), 3.19 ppm (d,˜54% of 2H, J=7.31 Hz), 3.37 ppm (d, ˜46% of 2H, J=7.41 Hz), 3.47 ppm(s, ˜54% of 3H), 3.57 ppm (s, ˜46% of 3H), 4.50-4.55 ppm (m, ˜46% of1H), 4.85 ppm (d, ˜54% of 1H, J=12.57 Hz, of t, J=7.31 Hz), 5.94 ppm (d,˜46% of 1H, J=6.12 Hz), 6.36 ppm (d, ˜54% of 1H, J=12.59 Hz), 7.03-7.10ppm (m, 4H)

The compound 4-methyl 1-(3-methoxy-2-propen-1-yl)benzene was describedas having muguet, green, and fatty notes.

Example IV

Preparation of 4-ethyl 1-(3-methoxy-2-propen-1-yl)benzene (Formula III):4-Ethyl 1-(3-methoxy-2-propen-1-yl)benzene was similarly prepared asdescribed in Examples I and II. First, 4-ethyl benzaldehyde (925 g,commercially available from Mitsubishi Gas Chemical Company, Inc.) wasused to obtain 3-(4-ethyl-phenyl)-propionaldehyde (878 g) with a boilingpoint of 129° C. at a pressure of 12 mmHg.3-(4-Ethyl-phenyl)-propionaldehyde (235 g) was consequently used toprovide 4-ethyl 1-(3-methoxy-2-propen-1-yl)benzene (128 g) with aboiling point of 120° C. at a pressure of 10 mmHg.

The NMR analysis of 3-(4-ethyl-phenyl)-propionaldehyde was thefollowing:

¹HNMR: 1.20 ppm (t, 3H, J=7.61 Hz), 2.59 ppm (q, 2H, J=7.58 Hz), 2.68ppm (t, 2H, J=7.55 Hz), 2.88 ppm (t, 2H, J=7.52 Hz), 7.06-7.11 ppm (m,4H), 9.73 ppm (s, 1H)

The NMR analysis of 4-ethyl 1-(3-methoxy-2-propen-1-yl)benzene was thefollowing:

¹HNMR: 1.20 ppm (t, ˜60% of 3H, J=7.59 Hz), 1.21 ppm (t, ˜40% of 3H,J=7.58 Hz), 2.56-2.63 ppm (m, 2H), 3.21 ppm (d, ˜40% of 2H, J=7.28 Hz),3.38 ppm (d, ˜60% of 2H, J=7.38 Hz), 3.48 ppm (s, ˜40% of 3H), 3.58 ppm(s, ˜60% of 3H), 4.52-4.57 ppm (m, ˜60% of 1H), 4.87 ppm (d, ˜40% of 1H,J=12.56 Hz, of t, J=7.28 Hz), 5.95 ppm (d, ˜60% of 1H, J=6.11 Hz), 6.37ppm (d, ˜40% of 1H, J=12.78 Hz), 7.07-7.13 ppm (m, 4H)

The compound 4-ethyl 1-(3-methoxy-2-propen-1-yl)benzene was described ashaving muguet, green, and fatty notes.

Example V

Preparation of 4-isobutyl 1-(3-methoxy-2-propen-1-yl)benzene (FormulaVIII): 4-Isobutyl 1-(3-methoxy-2-propen-1-yl)benzene was similarlyprepared as described in Examples I and II. First, 4-isobutylbenzaldehyde (600 g, commercially available from Mitsubishi Gas ChemicalCompany, Inc.) was used to obtain 3-(4-isobutyl-phenyl)-propionaldehyde(568 g) with a boiling point of 119° C. at a pressure of 5 mmHg.3-(4-Isobutyl-phenyl)-propionaldehyde (345 g) was consequently used toprovide 4-isobutyl 1-(3-methoxy-2-propen-1-yl)benzene (188 g) with aboiling point of 124° C. at a pressure of 4 mmHg.

The NMR analysis of 3-(4-isobutyl-phenyl)-propionaldehyde was thefollowing:

¹HNMR: 0.89 ppm (d, 6H, J=6.64 Hz), 1.83 ppm (m, 1H, J=6.74 Hz), 2.43ppm (d, 2H, J=7.18 Hz), 2.72 ppm (t, 2H, J=7.58 Hz, of d, J=1.15 Hz),2.90 ppm (t, 2H, J=7.57 Hz), 7.05 ppm (d, 2H, J=8.20 Hz), 7.08 ppm (d,2H, J=8.19 Hz), 9.77 ppm (t, 1H, J=1.43 Hz)

The NMR analysis of 4-isobutyl 1-(3-methoxy-2-propen-1-yl)benzene wasthe following:

¹HNMR: 0.89 ppm (d, ˜43% of 6H, J=6.59 Hz), 0.90 ppm (d, ˜57% of 6H,J=6.59 Hz), 1.81-1.86 ppm (m, 1H), 2.42-2.45 ppm (m, 2H), 3.23 ppm (d,˜57% of 2H, J=7.32 Hz), 3.39 ppm (d, ˜43% of 2H, J=7.40 Hz), 3.53 ppm(s, ˜57% of 3H), 3.63 ppm (s, ˜43% of 3H), 4.54-4.57 ppm (m, ˜43% of1H), 4.90 ppm (d, ˜57% of 1H, J=12.58 Hz, of t, J=7.32 Hz), 5.99 ppm (d,˜43% of 1H, J=6.13 Hz), 6.39 ppm (d, ˜57% of 1H, J=12.58 Hz), 7.03-7.07ppm (m, 2H), 7.10-7.13 ppm (m, 2H)

The compound 4-isobutyl 1-(3-methoxy-2-propen-1-yl)benzene was describedas having muguet, green, and fatty notes.

Example VI

Preparation of 4-tert-butyl 1-(3-methoxy-2-propen-1-yl)benzene (FormulaIX): 4-Tert-butyl 1-(3-methoxy-2-propen-1-yl)benzene was similarlyprepared as described in Examples I and II. First, 4-tert-butylbenzaldehyde (commercially available from TCI Company) was used toobtain 3-(4-tert-butyl-phenyl)-propionaldehyde (1.1 Kg), which wasconsequently used to afford 4-tert-butyl1-(3-methoxy-2-propen-1-yl)benzene (636 g). The product 4-tert-butyl1-(3-methoxy-2-propen-1-yl)benzene has a boiling point of 98° C. at apressure of 1.2 mmHg.

¹HNMR: 1.30 ppm (s, ˜40% of 9H), 1.31 ppm (s, ˜60% of 9H), 3.24 ppm (d,˜60% of 2H, J=7.36 Hz), 3.39 ppm (d, ˜40% of 2H, J=7.47 Hz), 3.53 ppm(s, ˜60% of 3H), 3.63 ppm (s, ˜40% of 3H), 4.54-4.59 ppm (m, ˜40% of1H), 4.90 ppm (d, ˜60% of 1H, J=12.58 Hz, of t, J=7.35 Hz), 5.99 ppm (d,˜40% of 1H, J=6.13 Hz), 6.40 ppm (d, ˜60% of 1H, J=12.59 Hz), 7.13-7.17ppm (m, 2H), 7.28-7.33 ppm (m, 2H)

The compound 4-tert-butyl 1-(3-methoxy-2-propen-1-yl)benzene wasdescribed as having muguet, green, and fatty notes.

Example VII

The fragrance formula exemplified as follows demonstrates that a 4-alkyl1-(3-methoxy-2-propen-1-yl)benzene compound imparts muguet and greencharacters to a musk fragrance formula.

Parts* Ingredients + − Allyl Caproate 10 10 Leaf Alcohol 5 5 Kharismal ®15 15 Seveniff ® 100 100 Alpha Damascone 5 5 Cashmeran ® 10 10Nebulone ® 50 50 Iso E Super ® 100 100 Phenoxanol ® 65 65 Vivaldie ® 2020 Verdox ® 70 70 Undecavertol 5 5 Applelide ® 40 40 4-Propyl1-(3-methoxy-2-propen-1-yl) benzene 45 — (Formula IV) DPG — 45 Total 540540 *“+” represents a 4-alkyl 1-(3-methoxy-2-propen-1-yl) benzenecompound containing formula; and “−” represents a 4-alkyl1-(3-methoxy-2-propen-1-yl) benzene compound non-containing formula.

Example VIII

The fragrance formula exemplified as follows demonstrates that a 4-alkyl1-(3-methoxy-2-propen-1-yl)benzene compound imparts muguet and greencharacters to a female fragrance formula.

Parts* Ingredients + − Salicynalva ® 80 80 Delta Damascone 25 25 GammaDecalactone 2 2 Dimethyloctenol 10 10 Phenyl ethyl alcohol 20 20Montaverdi ® 5 5 Geraniol 150 150 Linalool 50 50 Iso E Super ® 123 123Cashmeran ® 25 25 Applelide ® 100 100 Galbascone ® 15 15 Leaf Alcohol 55 Globanone ® 20 20 Aldehyde C10 30 30 Kharismal ® 25 25 Vanillin 5 54-Propyl 1-(3-methoxy-2-propen-1-yl) benzene 10 — (Formula IV) DPG — 10Total 700 700 *“+” represents a 4-alkyl 1-(3-methoxy-2-propen-1-yl)benzene compound containing formula; and “−” represents a 4-alkyl1-(3-methoxy-2-propen-1-yl) benzene compound non-containing formula.

1. A compound:

wherein R″ represents a C₂-C₄ alkyl group.
 2. The compound of claim 1,wherein the compound is 4-ethyl 1-(3-methoxy-2-propen-1-yl)benzene. 3.The compound of claim 1, wherein the compound is 4-propyl1-(3-methoxy-2-propen-1-yl)benzene.
 4. The compound of claim 1, whereinthe compound is 4-isopropyl 1-(3-methoxy-2-propen-1-yl)benzene.
 5. Thecompound of claim 1, wherein the compound is 4-butyl1-(3-methoxy-2-propen-1-yl)benzene.
 6. The compound of claim 1, whereinthe compound is 4-sec-butyl 1-(3-methoxy-2-propen-1-yl)benzene.
 7. Thecompound of claim 1, wherein the compound is 4-isobutyl1-(3-methoxy-2-propen-1-yl)benzene.
 8. The compound of claim 1, whereinthe compound is 4-tert-butyl 1-(3-methoxy-2-propen-1-yl)benzene.
 9. Afragrance formulation containing an olfactory effective amount of acompound:

wherein R″ represents a C₂-C₄ alkyl group.
 10. A fragrance productcontaining an olfactory effective amount of the compound:

wherein R″ represents a C₂-C₄ alkyl group.